PL208571B1 - Sposób wytwarzania 1,1,1,3,3- pentafluorobutanu - Google Patents
Sposób wytwarzania 1,1,1,3,3- pentafluorobutanuInfo
- Publication number
- PL208571B1 PL208571B1 PL385266A PL38526699A PL208571B1 PL 208571 B1 PL208571 B1 PL 208571B1 PL 385266 A PL385266 A PL 385266A PL 38526699 A PL38526699 A PL 38526699A PL 208571 B1 PL208571 B1 PL 208571B1
- Authority
- PL
- Poland
- Prior art keywords
- reaction
- hydrogen fluoride
- catalyst
- hydrofluorobutane
- mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 50
- 150000005828 hydrofluoroalkanes Chemical class 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 60
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 58
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims description 60
- 238000006243 chemical reaction Methods 0.000 claims description 53
- 239000002243 precursor Substances 0.000 claims description 42
- 239000003054 catalyst Substances 0.000 claims description 41
- 239000007791 liquid phase Substances 0.000 claims description 11
- FFBFEBDZFWMXBE-UHFFFAOYSA-N 1,1,1,3,3-pentachlorobutane Chemical group CC(Cl)(Cl)CC(Cl)(Cl)Cl FFBFEBDZFWMXBE-UHFFFAOYSA-N 0.000 claims description 10
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 6
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical group Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 5
- 150000003609 titanium compounds Chemical class 0.000 claims description 4
- -1 titanium halide Chemical class 0.000 claims description 4
- MRKAIYYTIQVWCK-UHFFFAOYSA-N 1,1-dichloro-1,3,3-trifluorobutane Chemical compound CC(F)(F)CC(F)(Cl)Cl MRKAIYYTIQVWCK-UHFFFAOYSA-N 0.000 claims description 3
- XPAUQCAVYXOWFR-UHFFFAOYSA-N 1,1-dichloro-1,3-difluorobut-2-ene Chemical compound CC(F)=CC(F)(Cl)Cl XPAUQCAVYXOWFR-UHFFFAOYSA-N 0.000 claims description 3
- JZKJJRVPJFNKMB-UHFFFAOYSA-N 1,3-dichloro-1,1,3-trifluorobutane Chemical compound CC(F)(Cl)CC(F)(F)Cl JZKJJRVPJFNKMB-UHFFFAOYSA-N 0.000 claims description 3
- DOSUCSMNYNCWBY-UHFFFAOYSA-N 1-chloro-1,1,3-trifluorobut-2-ene Chemical compound CC(F)=CC(F)(F)Cl DOSUCSMNYNCWBY-UHFFFAOYSA-N 0.000 claims description 3
- KQBWUCNIYWMKEK-UHFFFAOYSA-N 1-chloro-1-fluorobut-1-ene Chemical class CCC=C(F)Cl KQBWUCNIYWMKEK-UHFFFAOYSA-N 0.000 claims description 3
- HFZJRXWWTAKJAO-UHFFFAOYSA-N 3,3-dichloro-1,1,1-trifluorobutane Chemical compound CC(Cl)(Cl)CC(F)(F)F HFZJRXWWTAKJAO-UHFFFAOYSA-N 0.000 claims description 3
- BNUSKMGXRXIWAF-UHFFFAOYSA-N 3-chloro-1,1,1,3-tetrafluorobutane Chemical compound CC(F)(Cl)CC(F)(F)F BNUSKMGXRXIWAF-UHFFFAOYSA-N 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- SUKOXPHMFMJYRI-UHFFFAOYSA-N CC(C(C(Cl)(Cl)Cl)F)F Chemical class CC(C(C(Cl)(Cl)Cl)F)F SUKOXPHMFMJYRI-UHFFFAOYSA-N 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 7
- 150000001875 compounds Chemical group 0.000 abstract description 3
- 238000000605 extraction Methods 0.000 abstract 3
- 239000003960 organic solvent Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 1
- 238000004821 distillation Methods 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000007795 chemical reaction product Substances 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000003682 fluorination reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 3
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- BSERHUYXVAIRSG-UHFFFAOYSA-N 1-chloro-1,1,3,3-tetrafluorobutane Chemical compound CC(F)(F)CC(F)(F)Cl BSERHUYXVAIRSG-UHFFFAOYSA-N 0.000 description 2
- 241000183024 Populus tremula Species 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical class ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BCFNCPFDOWQWDP-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decachloropentane Chemical compound ClC(Cl)(Cl)C(Cl)C(Cl)C(Cl)(Cl)C(Cl)(Cl)Cl BCFNCPFDOWQWDP-UHFFFAOYSA-N 0.000 description 1
- HCCXTSAGOJXOJG-UHFFFAOYSA-N 1,1,1,3-tetrachloro-3-fluorobutane Chemical compound CC(F)(Cl)CC(Cl)(Cl)Cl HCCXTSAGOJXOJG-UHFFFAOYSA-N 0.000 description 1
- MINPZZUPSSVGJN-UHFFFAOYSA-N 1,1,1,4,4,4-hexachlorobutane Chemical compound ClC(Cl)(Cl)CCC(Cl)(Cl)Cl MINPZZUPSSVGJN-UHFFFAOYSA-N 0.000 description 1
- IZPMJFLFAHTFRK-UHFFFAOYSA-N 1,1,1-trichloro-3,3-difluorobutane Chemical compound CC(F)(F)CC(Cl)(Cl)Cl IZPMJFLFAHTFRK-UHFFFAOYSA-N 0.000 description 1
- XHDSPHHDGAQIDF-UHFFFAOYSA-N 1,1,3,3-tetrachloro-1-fluorobutane Chemical compound CC(Cl)(Cl)CC(F)(Cl)Cl XHDSPHHDGAQIDF-UHFFFAOYSA-N 0.000 description 1
- XQVOZHXFNGMERA-UHFFFAOYSA-N 1,1,3-trichloro-1,3-difluorobutane Chemical compound CC(F)(Cl)CC(F)(Cl)Cl XQVOZHXFNGMERA-UHFFFAOYSA-N 0.000 description 1
- RMDJNEOJTZWCJE-UHFFFAOYSA-N 1,3,3-trichloro-1,1-difluorobutane Chemical compound CC(Cl)(Cl)CC(F)(F)Cl RMDJNEOJTZWCJE-UHFFFAOYSA-N 0.000 description 1
- OUKWBMHBHGGKQE-UHFFFAOYSA-N 1-chloro-4,4,4-trifluorobut-1-ene Chemical class FC(F)(F)CC=CCl OUKWBMHBHGGKQE-UHFFFAOYSA-N 0.000 description 1
- DZDLBWDCTJUPKD-UHFFFAOYSA-N 3,3-dichloro-1,1-difluorobut-1-ene Chemical class CC(Cl)(Cl)C=C(F)F DZDLBWDCTJUPKD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/19—Fluorine; Hydrogen fluoride
- C01B7/191—Hydrogen fluoride
- C01B7/195—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/19—Fluorine; Hydrogen fluoride
- C01B7/191—Hydrogen fluoride
- C01B7/195—Separation; Purification
- C01B7/196—Separation; Purification by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE9800910 | 1998-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL208571B1 true PL208571B1 (pl) | 2011-05-31 |
Family
ID=3891577
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL385266A PL208571B1 (pl) | 1998-12-18 | 1999-12-16 | Sposób wytwarzania 1,1,1,3,3- pentafluorobutanu |
| PL385267A PL208572B1 (pl) | 1998-12-18 | 1999-12-16 | Sposób wytwarzania hydrofluoroalkanu, którym jest 1,1,1,3,3- pentafluorobutan |
| PL385268A PL206502B1 (pl) | 1998-12-18 | 1999-12-16 | Sposób wytwarzania 1, 1, 1, 3, 3-pentafluorobutanu |
| PL349391A PL200329B1 (pl) | 1998-12-18 | 1999-12-16 | Sposób rozdzielania mieszaniny zawierającej co najmniej jeden hydrofluoroalkan i fluorowodór oraz kompozycje azeotropowe lub pseudoazeotropowe |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL385267A PL208572B1 (pl) | 1998-12-18 | 1999-12-16 | Sposób wytwarzania hydrofluoroalkanu, którym jest 1,1,1,3,3- pentafluorobutan |
| PL385268A PL206502B1 (pl) | 1998-12-18 | 1999-12-16 | Sposób wytwarzania 1, 1, 1, 3, 3-pentafluorobutanu |
| PL349391A PL200329B1 (pl) | 1998-12-18 | 1999-12-16 | Sposób rozdzielania mieszaniny zawierającej co najmniej jeden hydrofluoroalkan i fluorowodór oraz kompozycje azeotropowe lub pseudoazeotropowe |
Country Status (19)
| Country | Link |
|---|---|
| US (4) | US6521803B1 (de) |
| EP (3) | EP2078708A1 (de) |
| JP (2) | JP4785251B2 (de) |
| KR (1) | KR100684939B1 (de) |
| CN (5) | CN1680232A (de) |
| AR (1) | AR021727A1 (de) |
| AT (1) | ATE430119T1 (de) |
| AU (1) | AU769820B2 (de) |
| BR (1) | BR9916345B1 (de) |
| CA (1) | CA2355385C (de) |
| CZ (1) | CZ303077B6 (de) |
| DE (1) | DE69940828D1 (de) |
| ES (1) | ES2325778T3 (de) |
| HU (1) | HU227729B1 (de) |
| PL (4) | PL208571B1 (de) |
| RU (2) | RU2261856C2 (de) |
| TW (1) | TW499407B (de) |
| WO (1) | WO2000037401A1 (de) |
| ZA (1) | ZA200104829B (de) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9916345B1 (pt) * | 1998-12-18 | 2011-08-23 | Processos de separação de uma mistura compreendendo pelo menos um hidrofluoroalcano e fluoreto de hidrogênio, de preparação de um hidrofluoroalcano, e, para a manufatura de 1,1,1,3,3,-pentafluorobutano. | |
| ATE428671T1 (de) * | 2001-06-01 | 2009-05-15 | Honeywell Int Inc | Azeotropähnliche zusammensetzungen aus 1,1,1,3,3- pentafluorbutan und fluorwasserstoff |
| US20030028057A1 (en) * | 2001-07-20 | 2003-02-06 | Stephen Owens | Methods and materials for the preparation and purification of halogenated hydrocarbons |
| US7094936B1 (en) * | 2001-07-20 | 2006-08-22 | Great Lakes Chemical Corporation | Process for preparing halogenated alkanes |
| FR2855069B1 (fr) * | 2003-05-22 | 2006-06-16 | Solvay | Procede pour la separation d'au moins un compose organique |
| US6988994B2 (en) * | 2003-08-14 | 2006-01-24 | New York University | Positive airway pressure system and method for treatment of sleeping disorder in patient |
| US8101219B2 (en) * | 2004-03-05 | 2012-01-24 | Eggology, Inc. | Apparatus for preparing egg products in a microwave oven |
| US7709438B2 (en) * | 2005-11-01 | 2010-05-04 | E. I. Du Pont De Nemours And Company | Azeotrope compositions comprising nonafluoropentene and hydrogen fluoride and uses thereof |
| US8766020B2 (en) * | 2008-07-31 | 2014-07-01 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US20070106099A1 (en) * | 2005-11-10 | 2007-05-10 | Pcbu Services, Inc. | Production processes and systems |
| RU2445302C2 (ru) | 2006-06-27 | 2012-03-20 | Е.И. Дюпон Де Немур Энд Компани | Способы получения тетрафторпропена |
| US7803975B2 (en) * | 2006-07-13 | 2010-09-28 | E.I. Du Pont De Nemours And Company | Process for separating a fluoroolefin from HF by liquid-liquid extraction |
| US9040759B2 (en) * | 2007-07-06 | 2015-05-26 | Honeywell International Inc. | Preparation of fluorinated olefins via catalytic dehydrohalogenation of halogenated hydrocarbons |
| CN101952230B (zh) * | 2008-02-21 | 2015-07-22 | 纳幕尔杜邦公司 | 通过共沸蒸馏使2,3,3,3-四氟丙烯与氟化氢分离的方法 |
| KR20200039844A (ko) * | 2008-02-21 | 2020-04-16 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 공비 증류에 의한 플루오르화수소로부터의 1,3,3,3-테트라플루오로프로펜의 분리 방법 |
| CN102015593B (zh) * | 2008-02-21 | 2015-06-03 | 纳幕尔杜邦公司 | 包含3,3,3-三氟丙烯与氟化氢的共沸组合物及其分离方法 |
| US8410040B2 (en) * | 2008-10-31 | 2013-04-02 | Honeywell International Inc. | Azeotrope-like compositions of 1,1,1,2,3-pentachloropropane and hydrogen fluoride |
| US8008243B2 (en) * | 2008-10-31 | 2011-08-30 | Honeywell International Inc. | Azeotrope-like compositions of 1,1,2,3-tetrachloropropene and hydrogen fluoride |
| EP2356086A2 (de) * | 2008-11-13 | 2011-08-17 | Solvay Fluor GmbH | Teilfluorierte olefine, herstellung von teilfluorierten olefinen und verfahren zur anwendung von teilfluorierten olefinen |
| CN102224123B (zh) * | 2008-11-25 | 2014-11-26 | 苏威氟有限公司 | 制备氯氟烯烃的方法 |
| US8093441B2 (en) * | 2008-12-18 | 2012-01-10 | Exxonmobil Research And Engineering Company | Removal of light fluoroalkanes from hydrocarbon streams |
| US8075797B2 (en) * | 2009-01-29 | 2011-12-13 | Honeywell International Inc. | Azeotrope-like compositions of pentafluoropropane, chlorotrifluoropropene, and hydrogen fluoride |
| TW201103972A (en) | 2009-04-01 | 2011-02-01 | Solvay Fluor Gmbh | Process for the manufacture of etched items |
| US8674147B2 (en) | 2010-04-02 | 2014-03-18 | Solvay Sa | Process for dehydrochlorination of hydrochlorofluoroalkanes |
| US8921622B2 (en) | 2010-04-02 | 2014-12-30 | Solvay Sa | Process for dehydrofluorinating hydrochlorofluoroalkanes and products obtained thereby |
| US8487155B2 (en) | 2010-12-07 | 2013-07-16 | Exxonmobil Research And Engineering Company | Removal of light fluoroalkanes from hydrocarbon streams |
| US8999909B2 (en) | 2012-02-23 | 2015-04-07 | Honeywell International Inc. | Azeotropic compositions of 1,1,1,3,3-pentachloropropane and hydrogen fluoride |
| CN111094503B (zh) * | 2017-09-11 | 2022-04-01 | 科慕埃弗西有限公司 | 包含氟化氢和含氟烃的共沸组合物 |
| CN110092707B (zh) * | 2018-01-30 | 2020-08-11 | 中昊晨光化工研究院有限公司 | 一种四氟乙烯生产过程中去除氟化氢的方法 |
| MY208986A (en) * | 2019-04-05 | 2025-06-14 | Chemours Co Fc Llc | Processes for producing z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same |
| JP6958596B2 (ja) * | 2019-07-01 | 2021-11-02 | ダイキン工業株式会社 | アルカンの製造方法 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1443616C3 (de) | 1963-11-13 | 1974-05-09 | Chemische Fabrik Von Heyden Gmbh, 8000 Muenchen | Verbessertes Verfahren zur Fluorierung und Polyfluorierung von Chlor enthaltenden niederen aliphatischen Halogenkohlenwasserstoffen |
| DE69031344D1 (de) * | 1989-10-04 | 1997-10-02 | Du Pont | Verfahren zur reinigung von fluorkohlenwasserstoffen |
| GB9007029D0 (en) * | 1990-03-29 | 1990-05-30 | Ici Plc | Chemical process |
| US5276225A (en) * | 1991-04-17 | 1994-01-04 | Elf Atochem S.A. | Process for separating hydrogen fluoride from its mixtures with 1,1,1-trifluoro-2-chloroethane |
| CA2111007C (en) * | 1992-04-13 | 2004-08-03 | Takehide Tsuda | Process for removal of hydrogen fluoride |
| IT1256631B (it) | 1992-12-10 | 1995-12-12 | Ausimont Spa | Procedimento per la separazione di hf da sue miscele con gli idroclorofluorcarburi 123 e/o 124 |
| US5395997A (en) * | 1993-07-29 | 1995-03-07 | Alliedsignal Inc. | Process for the preparation of hydrofluorocarbons having 3 to 7 carbon atoms |
| RU2065430C1 (ru) * | 1994-05-26 | 1996-08-20 | Российский научный центр "Прикладная химия" | Способ получения 1,1,1,3,3-пентафторпропана |
| US5414165A (en) * | 1994-07-29 | 1995-05-09 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,1,1,3,3,3,-hexafluoropropane |
| FR2724167B1 (fr) | 1994-09-05 | 1996-11-29 | Solvay | Procede pour l'hydrofluoration de chloro (fluoro) butane |
| RU2126396C1 (ru) | 1994-09-14 | 1999-02-20 | Сагами Кемикал Рисерч Сентр | Производные эпоксициклогексана и регуляторы роста растений |
| FR2724928B1 (fr) * | 1994-09-26 | 1996-10-31 | Atochem Elf Sa | Synthese de 1,1,1,3,3-pentafluoropropane |
| WO1997005089A1 (en) | 1995-08-01 | 1997-02-13 | E.I. Du Pont De Nemours And Company | Process for the manufacture of halocarbons and selected compounds and azeotropes with hf |
| US5616819A (en) * | 1995-08-28 | 1997-04-01 | Laroche Industries Inc. | Process for preparing fluorinated aliphatic compounds |
| CN1110449C (zh) * | 1995-10-10 | 2003-06-04 | 英尼奥斯费罗控股有限公司 | 分离和回收氟化氢的方法以及制备含氟有机化合物的方法 |
| FR2740132B1 (fr) | 1995-10-23 | 1997-12-19 | Solvay | Procede pour la preparation de 1,1,1,3,3-pentafluoropropane |
| FR2744442B1 (fr) * | 1996-02-01 | 1998-02-27 | Atochem Elf Sa | Preparation du 1,1,1,3,3-pentachlorobutane et du 1,1,1,3,3,-pentafluorobutane |
| JP3831987B2 (ja) * | 1996-09-25 | 2006-10-11 | 旭硝子株式会社 | 1,1,1,3,3−ペンタフルオロプロパンの製造方法 |
| US6023004A (en) * | 1996-11-12 | 2000-02-08 | Alliedsignal, Inc. | Liquid phase catalytic fluorination of hydrochlorocarbon and hydrochlorofluorocarbon |
| FR2768727A1 (fr) * | 1997-09-23 | 1999-03-26 | Atochem Elf Sa | Synthese du 1,1,1,3,3-pentafluoropropane |
| FR2768717B1 (fr) * | 1997-09-24 | 1999-11-12 | Solvay | Procede de separation de fluorure d'hydrogene de ses melanges avec un hydrofluoroalcane contenant de 3 a 6 atomes de carbone |
| BE1011765A3 (fr) * | 1998-02-26 | 2000-01-11 | Solvay | Procede d'hydrofluoration d'hydrocarbures. |
| BR9916345B1 (pt) * | 1998-12-18 | 2011-08-23 | Processos de separação de uma mistura compreendendo pelo menos um hidrofluoroalcano e fluoreto de hidrogênio, de preparação de um hidrofluoroalcano, e, para a manufatura de 1,1,1,3,3,-pentafluorobutano. | |
| ATE257814T1 (de) * | 1999-03-24 | 2004-01-15 | Solvay | Verfahren zur abtrennung von fluorwasserstoff aus seinen mischungen mit 1,1,1,3,3-pentafluorbutan und verfahren zur herstellung von pentafluorbutan |
| FR2791976B1 (fr) * | 1999-03-24 | 2001-07-27 | Solvay | Compositions contenant du fluorure d'hydrogene et du 1,1,1,3,3-pentafluorobutane, procede pour la separation de melanges comprenant de telles compositions et procede pour la synthese de 1,1,1,3,3-pentafluorobutane |
-
1999
- 1999-12-16 BR BRPI9916345-4A patent/BR9916345B1/pt not_active IP Right Cessation
- 1999-12-16 AT AT99967969T patent/ATE430119T1/de not_active IP Right Cessation
- 1999-12-16 CN CNA2005100651304A patent/CN1680232A/zh active Pending
- 1999-12-16 KR KR1020017007485A patent/KR100684939B1/ko not_active Expired - Fee Related
- 1999-12-16 CN CN2008100854764A patent/CN101284758B/zh not_active Expired - Lifetime
- 1999-12-16 EP EP09158967A patent/EP2078708A1/de not_active Ceased
- 1999-12-16 CN CNB998162469A patent/CN100387561C/zh not_active Ceased
- 1999-12-16 AU AU24333/00A patent/AU769820B2/en not_active Ceased
- 1999-12-16 CN CN201510305450.6A patent/CN104987277A/zh active Pending
- 1999-12-16 WO PCT/EP1999/010173 patent/WO2000037401A1/fr not_active Ceased
- 1999-12-16 PL PL385266A patent/PL208571B1/pl unknown
- 1999-12-16 US US09/868,368 patent/US6521803B1/en not_active Expired - Lifetime
- 1999-12-16 HU HU0104672A patent/HU227729B1/hu not_active IP Right Cessation
- 1999-12-16 RU RU2001119986/04A patent/RU2261856C2/ru not_active IP Right Cessation
- 1999-12-16 PL PL385267A patent/PL208572B1/pl unknown
- 1999-12-16 RU RU2005122401/04A patent/RU2392260C2/ru not_active IP Right Cessation
- 1999-12-16 DE DE69940828T patent/DE69940828D1/de not_active Expired - Lifetime
- 1999-12-16 CZ CZ20012215A patent/CZ303077B6/cs not_active IP Right Cessation
- 1999-12-16 ES ES99967969T patent/ES2325778T3/es not_active Expired - Lifetime
- 1999-12-16 EP EP99967969A patent/EP1140747B1/de not_active Expired - Lifetime
- 1999-12-16 JP JP2000589475A patent/JP4785251B2/ja not_active Expired - Fee Related
- 1999-12-16 PL PL385268A patent/PL206502B1/pl unknown
- 1999-12-16 PL PL349391A patent/PL200329B1/pl unknown
- 1999-12-16 AR ARP990106474A patent/AR021727A1/es not_active Application Discontinuation
- 1999-12-16 CN CNA2008100854779A patent/CN101284757A/zh active Pending
- 1999-12-16 EP EP11153263A patent/EP2368869A1/de not_active Withdrawn
- 1999-12-16 CA CA2355385A patent/CA2355385C/fr not_active Expired - Fee Related
- 1999-12-27 TW TW088123242A patent/TW499407B/zh not_active IP Right Cessation
-
2001
- 2001-06-13 ZA ZA200104829A patent/ZA200104829B/xx unknown
-
2002
- 2002-10-29 US US10/282,785 patent/US7074434B2/en not_active Expired - Fee Related
-
2006
- 2006-06-28 US US11/476,306 patent/US7223892B2/en not_active Expired - Fee Related
-
2007
- 2007-05-25 US US11/753,970 patent/US7566809B2/en not_active Expired - Fee Related
-
2009
- 2009-06-15 JP JP2009142392A patent/JP5144592B2/ja not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL208571B1 (pl) | Sposób wytwarzania 1,1,1,3,3- pentafluorobutanu | |
| US5616819A (en) | Process for preparing fluorinated aliphatic compounds | |
| JP3518321B2 (ja) | 1,1,1,3,3−ペンタフルオロプロパンの製造方法 | |
| JP3130657B2 (ja) | 1−クロロ−1,1,3,3,3− ペンタフルオロプロパン及び1,1,1,3,3,3−ヘキサフルオロプロパンの製造法 | |
| RU2114813C1 (ru) | Способы получения 1,1,1,3,3-пентафторпропана, способ получения 1,1,1,3,3-пентафтор-2-галогено-3-хлорпропана, способ получения 1,1,1,2,3,3-гексахлорпропена, способ получения 1,1,1,3,3-пентафтор-2,3-дихлорпропана | |
| JPWO1994014736A1 (ja) | 1,1,1,3,3‐ペンタフルオロプロパンの製造方法,及び1,1,1,3,3‐ペンタフルオロ‐2,3‐ジクロロプロパンの製造方法 | |
| JP3572619B2 (ja) | ジフルオロメタンの製造方法 | |
| JP3535563B2 (ja) | 水及びフルオロ炭化水素を含む共沸組成物、共沸蒸留により溶液から水を除去する方法及びハイドロフルオロアルカンの製造方法 | |
| AU2005306473B2 (en) | Process for production of 1,2,2,2-tetrafluoro ethyl difluoro methyl ether | |
| JPH1087524A (ja) | 1−クロロ−1,1−ジフルオロエタンのフッ素化による1,1,1−トリフルオロエタンの合成 | |
| AU4597700A (en) | Production of 1,1,1,2,3,3,3-heptafluoropropane | |
| US5434320A (en) | Process for preparing dichlorofluoroethane and chlorodifluoroethane | |
| MXPA01006206A (en) | Method for separating a mixture comprising at least an hydrofluoroalkane and hydrogen fluoride, methods for preparing a hydrofluoroalkane and azeotropic compositions | |
| JPH0324025A (ja) | 弗化水素と1,1,1―トリクロロエタンを液相で連続反応させ、1,1―ジクロロ―1フルオロエタン及び1―クロロ―1,1―ジフルオロエタンの混合物を提供する為の製造方法 |